CN107400136B - 2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine and preparation method thereof - Google Patents

2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine and preparation method thereof Download PDF

Info

Publication number
CN107400136B
CN107400136B CN201610344856.XA CN201610344856A CN107400136B CN 107400136 B CN107400136 B CN 107400136B CN 201610344856 A CN201610344856 A CN 201610344856A CN 107400136 B CN107400136 B CN 107400136B
Authority
CN
China
Prior art keywords
pyrimidine
compound
triazol
dihydro
methylthiopyrimidine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201610344856.XA
Other languages
Chinese (zh)
Other versions
CN107400136A (en
Inventor
王涛
熊飞
熊更明
吴小盛
赵安林
余维洁
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangxi Normal University
Original Assignee
Jiangxi Normal University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangxi Normal University filed Critical Jiangxi Normal University
Priority to CN201610344856.XA priority Critical patent/CN107400136B/en
Publication of CN107400136A publication Critical patent/CN107400136A/en
Application granted granted Critical
Publication of CN107400136B publication Critical patent/CN107400136B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems

Abstract

2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazols [1,5-c] pyrimidine and preparation method thereof, general structure are as follows:In formula, R1Indicate alkyl；R2It indicates to replace chlorine；R3Indicate alkyl.Compound of the present invention with general structure I has significant inhibiting effect to the growth of unifacial leaf or dicotyledon, can be used as the effective component of herbicide.

Description

2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] is phonetic Pyridine and preparation method thereof
Technical field
The present invention relates to the 2- substituted benzene oxygen methylene -5- alkyl -4,6- dihydro -8- alkylthio group -10- with activity of weeding Methylthiopyrimidine simultaneously [5,4-e] -1,2,4- triazols [1,5-c] pyrimidine and preparation method thereof and its life as herbicide Object activity.
Background technique
Pyrimidine (C4H4N2, 1,3- diazine) and it is a kind of heterocyclic compound.By in 2 nitrogen-atoms substituted benzene molecule meta positions 2 carbon formed, be a kind of diazine.As pyridine, pyrimidine remains armaticity.Can it replace on its four carbon And generate the derivative of pyrimidine.The special construction of pyrimidine makes it have bioactivity not available for other structures, such as pest-resistant Antibacterial kills mouse weeding etc..Pyrimidine is also through having very extensive utilization prospect frequently as the intermediate for synthesizing other compounds.
Pyrimidines and its derivative play an important role in vivo, are a kind of active with good biological Heterocyclic compound.Pyrimidine is widely used in antibiotic as intermediate, and hypnotic sedative agent and novel spraying are that ultra high efficiency is removed suddenly The synthesis of careless agent.People had found that some drugs containing pyrimidine ring had antitumor activity again in recent years, and such as: nitric acid is phonetic Pyridine mustargen series antineoplastic medicament, selectivity height, low toxin wide with anticancer spectrum, and clinically obtained extensive Using.Thiourea containing pyrimidine ring is commonly used for fungicide.Thiourea is since there are different substitutions in structure Peptide bond (CONH), therefore with the antibiotic property of wide spectrum and pesticidal
Pyrimidine structure is with having a extensive future, so the method for finding fast and simple synthesis pyrimidine is very significant.Pyrimidine And its derivative is one kind important in heterocyclic compound, is a variety of drugs, pesticide, fragrance and the intermediate of organic synthesis, it is phonetic The optimization and improvement of pyridine synthetic method will greatly promote the development of related industry.The synthetic method of pyrimidine and aromatic ring substituted pyrimidines has Many reports, the synthetic method of the latter one are broadly divided into two classes, and one kind is that pyrimidine is generated by cyclization reaction, another kind of to be It is introduced directly into required functional group on the compound that oneself has pyrimidine structure or exchanges functional group on pyrimidine derivatives.
Summary of the invention
The object of the present invention is to provide a kind of 2- substituted benzene oxygen methylene -5- alkyl -4,6- dihydro -8- alkylthio group -10- first Sulfenyl pyrimido [5,4-e] -1,2,4- triazols [1,5-c] pyrimidine and preparation method thereof, exploring has new construction and with removing The active polysubstituted pyrimidine derivative of grass.
It adopts the technical scheme that achieve the purpose of the present invention:
(1) 2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] the pyrimidine structure general formula Such as I:
In formula: R1Indicate ethyl, n-propyl, normal-butyl；R2Adjacent chlorine is indicated, to chlorine, adjacency pair dichloro；R3Indicate methyl, second Base, n-propyl, isopropyl, normal-butyl, isobutyl group.
(2) 2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] the pyrimidine preparation method Be: the triazole for being II with general formula joins pyrimidine and fatty aldehyde reaction generates the compound that general formula is I, and ethyl alcohol is as solvent system It is standby；
The synthetic route of the compound indicated with general formula I is as follows:
The R that general formula is II1、R2Definition and R in the general structure I1、R2Definition it is identical.
II and fatty aldehyde molar ratio in above-mentioned reaction equation are 1:1.2, back flow reaction 3-4 hours in ethanol, can be obtained To preferable yield.
Beneficial effects of the present invention: 2- substituted benzene oxygen methylene -5- alkyl -4,6- dihydro -8- alkylthio group -10- methyl mercapto Pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine has significant inhibit to the growth of unifacial leaf and dicotyledon Effect, can be used as the effective component of herbicide.
Specific embodiment
The preparation method of formula work compound of the invention is specifically described below by example, these embodiments are only right The present invention is illustrated, rather than is limited the invention.
The preparation of 1 compound 1 of embodiment
2- benzene Oxymethylene -5- methyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- three Azoles simultaneously [1,5-c] pyrimidine
Phonetic triazole connection pyrimidine compound is taken 2.5mmol (about 1g), catalyst zirconium chloride 1.25mmol (50mol%), It takes 20mL dehydrated alcohol to dissolve, 3mmol (1:1.2) fatty aldehyde is added into system.3-4 is small back for entire reaction process stirring When.In reaction process, faint yellow solid Precipitation is had, which is the pyrimido-pyrimidine band triazole bone that we need The compound of frame.Yield is 75%, m.p.212-223 DEG C.
C18H20N6OS2
IR(KBr,υ/cm-1): 2962,2931,1529,1452,681
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 5H), 5.24 (s, 2H), 3.16-3.05 (m, 2H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 4H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 400 (M+)；Anal.Calcd. (%) for C16H20N6OS2:C,53.98；H,5.03；N, 20.98；found:C,53.96；H,5.02；N,20.99
Following 53 compounds are made by the similar method of compound 1, and Structural Identification data are as follows:
Compound 2
2- benzene Oxymethylene -5- ethyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- three Azoles simultaneously [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 78%, m.p.235-236 DEG C
C19H22N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 5H), 5.24 (s, 2H), 3.16-3.05 (m, 4H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 4H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 414 (M+)；Anal.Calcd. (%) for C19H22N6OS2:C,55.05；H,5.35；N, 20.27；found:C,55.03；H,5.34；N,20.29
Compound 3
2- benzene Oxymethylene -5- n-propyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 76%, m.p.242-243 DEG C
C20H24N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 5H), 5.24 (s, 2H), 3.16-3.05 (m, 6H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 4H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 428 (M+)；Anal.Calcd. (%) for C20H24N6OS2:C,56.05；H,5.64；N, 19.61；found:C,56.07；H,5.63；N,19.60
Compound 4
2- benzene Oxymethylene -5- isopropyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 81%, m.p.232-233 DEG C
C20H24N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 5H), 5.24 (s, 2H), 3.16-3.05 (m, 6H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 4H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 428 (M+)；Anal.Calcd. (%) for C20H24N6OS2:C,56.05；H,5.64；N, 19.61；found:C,56.06；H,5.62；N,19.62
Compound 5
2- benzene Oxymethylene -5- normal-butyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 72%, m.p.256-258 DEG C
C21H26N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 5H), 5.24 (s, 2H), 3.16-3.05 (m, 8H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 4H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 442 (M+)；Anal.Calcd. (%) for C21H26N6OS2:C,56.99；H,5.92；N, 18.99；found: C,56.97；H,5.93；N,19.01；
Compound 6
2- benzene Oxymethylene -5- isobutyl group -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 77%, m.p.251-253 DEG C
C21H26N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 5H), 5.24 (s, 2H), 3.16-3.05 (m, 5H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 4H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 442 (M+)；Anal.Calcd. (%) for C21H26N6OS2:C,56.99；H,5.92；N, 18.99；found: C,56.98；H,5.94；N,19.00；
Compound 7
2- to chlorobenzene Oxymethylene -5- methyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1,2, 4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 72%, m.p.261-262 DEG C
C18H19ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 2H), 3.16-3.05 (m, 1H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 2H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 434 (M+)；Anal.Calcd. (%) for C18H19ClN6OS2:C,49.70；H,4.40； N,19.32；found: C,49.73；H,4.41；N,19.28
Compound 8
2- to chlorobenzene Oxymethylene -5- ethyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1,2, 4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 75%, m.p.267-269 DEG C
C19H21ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 2H), 3.16-3.05 (m, 1H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 4H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 448 (M+)；Anal.Calcd. (%) for C19H21ClN6OS2:C,50.83；H,4.71； N,18.72；found: C,50.85；H,4.70；N,18.70
Compound 9
2- to chlorobenzene Oxymethylene -5- n-propyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 77%, m.p.272-273 DEG C
C20H23ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 2H), 3.16-3.05 (m, 1H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 6H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 462 (M+)；Anal.Calcd. (%) for C20H23ClN6OS2:C,51.88；H,5.01； N,18.15；found: C,51.89；H,5.00；N,18.17
Compound 10
2- to chlorobenzene Oxymethylene -5- isopropyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 87%, m.p.263-264 DEG C
C20H23ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 2H), 3.16-3.05 (m, 1H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 9H)
MS (EI, m/z, %): 462 (M+)；Anal.Calcd. (%) for C20H23ClN6OS2:C,51.88；H,5.01； N,18.15；found: C,51.86；H,5.04；N,18.19
Compound 11
2- to chlorobenzene Oxymethylene -5- normal-butyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 74%, m.p.287-289 DEG C
C21H25ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 2H), 3.16-3.05 (m, 3H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 6H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 476 (M+)；Anal.Calcd. (%) for C21H25ClN6OS2:C,52.87；H,5.28； N,17.62；found: C,52.89；H,5.29；N,17.60
Compound 12
2- to chlorobenzene Oxymethylene -5- isobutyl group -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 79%, m.p.277-279 DEG C
C21H25ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 2H), 3.16-3.05 (m, 3H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 9H)
MS (EI, m/z, %): 476 (M+)；Anal.Calcd. (%) for C21H25ClN6OS2:C,52.87；H,5.28； N,17.62；found: C,52.90；H,5.29；N,17.57
Compound 13
2- (2,4 dichloro benzene Oxymethylene) -5- methyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4- E] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 63%, m.p.272-274 DEG C
C18H18Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 2H), 3.16-3.05 (m, 3H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 468 (M+)；Anal.Calcd. (%) for C18H18Cl2N6OS2:C,46.06；H,3.87； N,17.90；found: C,46.08；H,3.89；N,17.85
Compound 14
2- (2,4 dichloro benzene Oxymethylene) -5- ethyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5,4- E] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 66%, m.p.279-280 DEG C
C19H20Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 2H), 3.16-3.05 (m, 4H), 2.51 (s, 4H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 482 (M+)；Anal.Calcd. (%) for C19H20Cl2N6OS2:C,47.20；H,4.17； N,17.38；found: C,47.23；H,4.20；N,17.32
Compound 15
2- (2,4 dichloro benzene Oxymethylene) -5- n-propyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 72%, m.p.287-289 DEG C
C20H22Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 2H), 3.16-3.05 (m, 4H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 496 (M+)；Anal.Calcd. (%) for C20H22Cl2N6OS2:C,48.29；H,4.46； N,16.89；found: C,48.26；H,4.43；N,16.93
Compound 16
2- (2,4 dichloro benzene Oxymethylene) -5- isopropyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 82%, m.p.280-282 DEG C
C20H22Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 2H), 3.16-3.05 (m, 4H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 496 (M+)；Anal.Calcd. (%) for C20H22Cl2N6OS2:C,48.29；H,4.46； N,16.89；found: C,48.24；H,4.46；N,16.93
Compound 17
2- (2,4 dichloro benzene Oxymethylene) -5- normal-butyl -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 77%, m.p.293-295 DEG C
C21H24Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 4H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 3H)
MS (EI, m/z, %): 510 (M+)；Anal.Calcd. (%) for C21H24Cl2N6OS2:C,49.31；H,4.73； N,16.43；found: C,49.34；H,4.75；N,16.40
Compound 18
2- (2,4 dichloro benzene Oxymethylene) -5- isobutyl group -4,6- dihydro -8- ethylmercapto group -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 81%, m.p.288-289 DEG C
C21H24Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 4H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 510 (M+)；Anal.Calcd. (%) for C21H24Cl2N6OS2:C,49.31；H,4.73； N,16.43；found: C,49.36；H,4.72；N,16.43
Compound 19
2- benzene Oxymethylene -5- methyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- three Azoles simultaneously [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 69%, m.p.258-259 DEG C
C19H22N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 2H), 3.16-3.05 (m, 4H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 414 (M+)；Anal.Calcd. (%) for C19H22N6OS2:C,55.05；H,5.35；N, 20.27；found: C,55.03；H,5.33；N,20.30
Compound 20
2- benzene Oxymethylene -5- ethyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- three Azoles simultaneously [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 74%, m.p.262-263 DEG C
C20H24N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 4H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 428 (M+)；Anal.Calcd. (%) for C20H24N6OS2:C,56.05；H,5.64；N, 19.61；found: C,56.01；H,5.60；N,19.69
Compound 21
2- benzene Oxymethylene -5- n-propyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 77%, m.p.269-271 DEG C
C21H26N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 6H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 442 (M+)；Anal.Calcd. (%) for C21H26N6OS2:C,56.99；H,5.92；N, 18.99；found: C,56.97；H,5.91；N,19.02
Compound 22
2- benzene Oxymethylene -5- isopropyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 86%, m.p.259-261 DEG C
C21H26N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 6H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 442 (M+)；Anal.Calcd. (%) for C21H26N6OS2:C,56.99；H,5.92；N, 18.99；found: C,56.97；H,5.91；N,19.02
Compound 23
2- benzene Oxymethylene -5- normal-butyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 79%, 300 DEG C of m.p. >
C22H28N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 6H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 456 (M+)；Anal.Calcd. (%) for C21H26N6OS2:C,57.87；H,6.18；N, 18.40；found: C,57.89；H,6.14；N,18.45；
Compound 24
2- benzene Oxymethylene -5- normal-butyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 83%, 300 DEG C of m.p. >
C22H28N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 6H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 456 (M+)；Anal.Calcd. (%) for C21H26N6OS2:C,57.87；H,6.18；N, 18.40；found: C,57.89；H,6.14；N,18.45；
Compound 25
2- to chlorobenzene Oxymethylene -5- methyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1,2, 4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 62%, 300 DEG C of m.p. >
C19H21ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 2H), 3.16-3.05 (m, 3H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 448 (M+)；Anal.Calcd. (%) for C19H21ClN6OS2:C,50.83；H,4.71； N,18.72；found:C,50.80；H,4.70；N,18.76
Compound 26
2- to chlorobenzene Oxymethylene -5- ethyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1,2, 4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 63%, 300 DEG C of m.p. >
C20H23ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 462 (M+)；Anal.Calcd. (%) for C20H23ClN6OS2:C,51.88；H,5.01； N,18.15；found:C,51.86；H,5.00；N,18.18
Compound 27
2- to chlorobenzene Oxymethylene -5- n-propyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 73%, 300 DEG C of m.p. >
C21H25ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 476 (M+)；Anal.Calcd. (%) for C21H25ClN6OS2:C,52.87；H,5.28； N,17.62；found:C,52.89；H,5.26；N,17.60
Compound 28
2- to chlorobenzene Oxymethylene -5- isopropyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 83%, 300 DEG C of m.p. >
C21H25ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 2H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 476 (M+)；Anal.Calcd. (%) for C21H25ClN6OS2:C,52.87；H,5.28； N,17.62；found:C,52.89；H,5.26；N,17.60
Compound 29
2- to chlorobenzene Oxymethylene -5- normal-butyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 78%, 300 DEG C of m.p. >
C22H27ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 6H), 3.16-3.05 (m, 4H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 490 (M+)；Anal.Calcd. (%) for C22H27ClN6OS2:C,53.81；H,5.54； N,17.11；found:C,53.83；H,5.56；N,17.10
Compound 30
2- to chlorobenzene Oxymethylene -5- isobutyl group -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 82%, 300 DEG C of m.p. >
C22H27ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 4H), 5.24 (s, 6H), 3.16-3.05 (m, 4H), 2.51 (s, 3H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 490 (M+)；Anal.Calcd. (%) for C22H27ClN6OS2:C,53.81；H,5.54； N,17.11；found:C,53.83；H,5.56；N,17.10
Compound 31
2- (2,4 dichloro benzene Oxymethylene) -5- methyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4- E] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 75%, 300 DEG C of m.p. >
C19H20Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 2H), 3.16-3.05 (m, 3H), 2.51 (s, 2H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 482 (M+)；Anal.Calcd. (%) for C19H20Cl2N6OS2:C,47.20；H,4.17； N,17.38；found:C,47.22；H,4.19；N,17.35
Compound 32
2- (2,4 dichloro benzene Oxymethylene) -5- ethyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5,4- E] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 71%, 300 DEG C of m.p. >
C20H22Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 2H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 496 (M+)；Anal.Calcd. (%) for C20H22Cl2N6OS2:C,48.29；H,4.46； N,16.89；found:C,48.31；H,4.48；N,16.87
Compound 33
2- (2,4 dichloro benzene Oxymethylene) -5- n-propyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 78%, 300 DEG C of m.p. >
C21H24Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 4H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 510 (M+)；Anal.Calcd. (%) for C21H24Cl2N6OS2:C,49.31；H,4.73； N,16.43；found:C,49.34；H,4.70；N,16.42
Compound 34
2- (2,4 dichloro benzene Oxymethylene) -5- isopropyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 82%, 300 DEG C of m.p. >
C21H24Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 4H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 510 (M+)；Anal.Calcd. (%) for C21H24Cl2N6OS2:C,49.31；H,4.73； N,16.43；found:C,49.34；H,4.70；N,16.42
Compound 35
2- (2,4 dichloro benzene Oxymethylene) -5- normal-butyl -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 75%, 300 DEG C of m.p. >
C22H26Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 4H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 524 (M+)；Anal.Calcd. (%) for C22H26Cl2N6OS2:C,50.28；H,4.99； N,15.99；found:C,50.26；H,4.98；N,16.02
Compound 36
2- (2,4 dichloro benzene Oxymethylene) -5- isobutyl group -4,6- dihydro -8- rosickyite base -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 79%, 300 DEG C of m.p. >
C22H26Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 4H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 524 (M+)；Anal.Calcd. (%) for C22H26Cl2N6OS2:C,50.28；H,4.99； N,15.99；found:C,50.26；H,4.98；N,16.02
Compound 37
2- benzene Oxymethylene -5- methyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- three Azoles simultaneously [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 67%, 300 DEG C of m.p. >
C20H24N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 4H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 428 (M+)；Anal.Calcd. (%) for C20H24N6OS2:C,56.05；H,5.64；N, 19.61；found: C,56.04；H,5.63；N,19.62
Compound 38
2- benzene Oxymethylene -5- ethyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- three Azoles simultaneously [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 71%, 300 DEG C of m.p. >
C21H26N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 442 (M+)；Anal.Calcd. (%) for C21H26N6OS2:C,56.99；H,5.92；N, 18.99；found: C,56.98；H,5.94；N,18.97
Compound 39
2- benzene Oxymethylene -5- n-propyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 76%, 300 DEG C of m.p. >
C22H28N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 456 (M+)；Anal.Calcd. (%) for C22H28N6OS2:C,57.87；H,6.18；N, 18.40；found: C,57.86；H,6.16；N,18.44
Compound 40
2- benzene Oxymethylene -5- isopropyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 72%, 300 DEG C of m.p. >
C22H28N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 456 (M+)；Anal.Calcd. (%) for C22H28N6OS2:C,57.87；H,6.18；N, 18.40；found: C,57.86；H,6.16；N,18.44
Compound 41
2- benzene Oxymethylene -5- normal-butyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 79%, 300 DEG C of m.p. >
C23H30N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 470 (M+)；Anal.Calcd. (%) for C23H30N6OS2:C,58.69；H,6.42；N, 17.86；found: C,58.66；H,6.43；N,17.88
Compound 42
2- benzene Oxymethylene -5- normal-butyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1,2,4- Triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 80%, 300 DEG C of m.p. >
C23H30N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 470 (M+)；Anal.Calcd. (%) for C23H30N6OS2:C,58.69；H,6.42；N, 17.86；found: C,58.66；H,6.43；N,17.88
Compound 43
2- to chlorobenzene Oxymethylene -5- methyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1,2, 4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 80%, 300 DEG C of m.p. >
C20H23ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 2H), 3.16-3.05 (m, 2H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 462 (M+)；Anal.Calcd. (%) for C20H23ClN6OS2:C,51.88；H,5.01； N,18.15；found:C,51.86；H,5.00；N,18.17
Compound 44
2- to chlorobenzene Oxymethylene -5- ethyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1,2, 4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 71%, 300 DEG C of m.p. >
C21H25ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 2H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 476 (M+)；Anal.Calcd. (%) for C21H25ClN6OS2:C,52.87；H,5.28； N,17.62；found:C,52.86；H,5.27；N,17.65
Compound 45
2- to chlorobenzene Oxymethylene -5- n-propyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 71%, 300 DEG C of m.p. >
C22H27ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 2H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 490 (M+)；Anal.Calcd. (%) for C22H27ClN6OS2:C,53.81；H,5.54； N,17.11；found:C,53.80；H,5.52；N,17.15
Compound 46
2- to chlorobenzene Oxymethylene -5- isopropyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 73%, 300 DEG C of m.p. >
C22H27ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 2H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 490 (M+)；Anal.Calcd. (%) for C22H27ClN6OS2:C,53.81；H,5.54； N,17.11；found:C,53.80；H,5.52；N,17.15
Compound 47
2- to chlorobenzene Oxymethylene -5- normal-butyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 78%, 300 DEG C of m.p. >
C23H29ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 4H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 504 (M+)；Anal.Calcd. (%) for C23H29ClN6OS2:C,54.69；H,5.79； N,16.64；found:C,54.66；H,5.78；N,16.69
Compound 48
2- to the different Ding Ji -4,6- dihydro -8- butylthio -10- methylthiopyrimidine of chlorobenzene Oxymethylene -5- simultaneously [5,4-e] -1, 2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 78%, 300 DEG C of m.p. >
C23H29ClN6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 4H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 504 (M+)；Anal.Calcd. (%) for C23H29ClN6OS2:C,54.69；H,5.79； N,16.64；found:C,54.66；H,5.78；N,16.69
Compound 49
2- (2,4 dichloro benzene Oxymethylene) -5- methyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4- E] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 79%, 300 DEG C of m.p. >
C20H22Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 2H), 3.16-3.05 (m, 3H), 2.51 (s, 4H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 496 (M+)；Anal.Calcd. (%) for C20H22Cl2N6OS2:C,48.29；H,4.46； N,16.89；found:C,48.28；H,4.45；N,16.92
Compound 50
2- (2,4 dichloro benzene Oxymethylene) -5- ethyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5,4- E] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 81%, 300 DEG C of m.p. >
C21H24Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 4H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 510 (M+)；Anal.Calcd. (%) for C21H24Cl2N6OS2:C,49.31；H,4.73； N,16.43；found:C,49.33；H,4.75；N,16.40
Compound 51
2- (2,4 dichloro benzene Oxymethylene) -5- n-propyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 77%, 300 DEG C of m.p. >
C22H26Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 524 (M+)；Anal.Calcd. (%) for C22H26Cl2N6OS2:C,50.28；H,4.99； N,15.99；found:C,50.26；H,4.97；N,16.02
Compound 52
2- (2,4 dichloro benzene Oxymethylene) -5- isopropyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 79%, 300 DEG C of m.p. >
C22H26Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 4H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 524 (M+)；Anal.Calcd. (%) for C22H26Cl2N6OS2:C,50.28；H,4.99； N,15.99；found:C,50.26；H,4.97；N,16.02
Compound 53
2- (2,4 dichloro benzene Oxymethylene) -5- normal-butyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 75%, 300 DEG C of m.p. >
C23H28Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 538 (M+)；Anal.Calcd. (%) for C23H28Cl2N6OS2:C,51.20；H,5.23； N,15.58；found:C,51.22；H,5.25；N,15.54
Compound 54
2- (2,4 dichloro benzene Oxymethylene) -5- normal-butyl -4,6- dihydro -8- butylthio -10- methylthiopyrimidine simultaneously [5, 4-e] -1,2,4- triazol [1,5-c] pyrimidine
Gained sterling be yellow solid, yield 75%, 300 DEG C of m.p. >
C23H28Cl2N6OS2
1H NMR (400MHz, DMSO) δ 8.67 (s, 1H), 7.41-7.84 (q, J=8.6Hz, 3H), 5.24 (s, 6H), 3.16-3.05 (m, 3H), 2.51 (s, 6H), 1.68 (dd, J=18.0,6.6Hz, 3H), 0.99 (t, J=7.3Hz, 6H)
MS (EI, m/z, %): 538 (M+)；Anal.Calcd. (%) for C23H28Cl2N6OS2:C,51.20；H,5.23； N,15.58；found:C,51.22；H,5.25；N,15.54
Using above-mentioned similar method, other compounds can be prepared.Listed in following table is the change of the invention synthesized Close object.
The compound of synthesis
The compound of formula 1 be made granula, hydrating agents, emulsion, flowable dose come using.It can also be with other weedings Agent, insecticide, kills and hides agent, plant growth regulator, fertilizer and soil conditioner from and be used in mixed way or be used in combination simultaneously at fungicide.
Embodiment 2
Activity of weeding experiment
Experimental material
Electronic balance one, beaker, dropper, pipette, ear washing bulb, culture dish, circular filter paper, graduated scale, distilled water, DMF, emulsifier (Tween-80), sample to be tested.
Test plant is, radish [Radish, Dan Yezi weeds (Monocotyledonous weeds)], rape [Rape, Broadleaf weed (Dicotyledonous weeds)].
Test method
Activity of weeding is tested using in vitro culture ware.
With electronic balance weighing 3-5mg sample to be tested, 0.5mL DMF dissolution is added, 1 drop emulsifier (Tween-80) is added dropwise, Add 3-5mL distilled water (sample how many milligram just add few milliliter of distilled water) to be made into the solution of 1000mg/L, takes this solution 1mL Add distilled water to be diluted to 10mL, that is, is made into the sample solution of 100mg/mL, the sample solution of 1mL 100mg/mL is equally taken to add steaming Distilled water is diluted to 10mL, that is, is made into the sample solution of 10mg/mL.The culture dish for being 9cm with diameter, built-in two layers of filter paper and 15- 20 rapes, radish seed, the sample solution for being separately added into 100mg/mL (100ppm) and 10mg/mL (10 ppm) cultivates Liquid.In aforementioned manners, not medication sample solution, directly makees culture solution with distilled water, makees blank control, covers culture dish upper cover.It will Culture dish lies in a horizontal plane in artificial incubator and cultivates, and temperature is 25 DEG C, and after culture three days, daily illumination 8 hours is handled 8 days Investigation test situation afterwards.The length for measuring plant root and stem, takes wherein 10 plants of mean value calculation result.As a result it is positive and illustrates medicine Agent is inhibited, illustrates that medicament has facilitation for negative value.
Effect=[(blank average length-processing average length)/blank average length] * 100
Activity criteria: A grades:>=90%B grades:>=70%C grades:>=50%D grades:<50%
Test result is as follows:
Inhibitory activity data of the compound to single, double cotyledon plant
Inhibitory activity data (culture dish method) of the compound to single, double cotyledon plant.

Claims (2)

1.2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine, it is characterized in that:
2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] the pyrimidine structure general formula such as I:
In formula: R1Indicate ethyl, n-propyl, normal-butyl；R2Adjacent chlorine is indicated, to chlorine, adjacency pair dichloro；R3Expression methyl, ethyl, just Propyl, isopropyl, normal-butyl, isobutyl group.
The preparation method of 2.2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine, feature Be: the triazole for being II with general formula joins pyrimidine and fatty aldehyde reaction generates the compound that general formula is I, and ethyl alcohol is as solvent system It is standby；
The synthetic route of the compound indicated with general formula I is as follows:
The R that general formula is II1、R2Definition and claim in 1 the general structure I in R1、R2Definition it is identical；General formula II With general formula I and compound R3R in-CHO3For methyl, ethyl, n-propyl, isopropyl, normal-butyl or isobutyl group；Above-mentioned reaction In formula II with fatty aldehyde molar ratio be 1:1.2, back flow reaction 3-4 hours in ethanol.
CN201610344856.XA 2016-05-22 2016-05-22 2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine and preparation method thereof Active CN107400136B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610344856.XA CN107400136B (en) 2016-05-22 2016-05-22 2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610344856.XA CN107400136B (en) 2016-05-22 2016-05-22 2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine and preparation method thereof

Publications (2)

Publication Number Publication Date
CN107400136A CN107400136A (en) 2017-11-28
CN107400136B true CN107400136B (en) 2019-11-29

Family

ID=60389199

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610344856.XA Active CN107400136B (en) 2016-05-22 2016-05-22 2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine and preparation method thereof

Country Status (1)

Country Link
CN (1) CN107400136B (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102399225A (en) * 2011-11-28 2012-04-04 江西师范大学 3-fluorine-containing substituted benzamido-3,4-dihydro-4-imide-5-methylthio-7-ethylthio pyrimido[4,5-d]pyrimidine with herbicidal activity and preparation method thereof
CN102399226A (en) * 2011-11-28 2012-04-04 江西师范大学 3-substituted benzamido-3,4-dihydro-4-imine-5-methylmercapto-7-alkylthio pyrimido [4,5-d] pyrimidine with herbicidal activity and preparation method thereof
CN102491977A (en) * 2011-11-28 2012-06-13 江西师范大学 1-substituted benzene oxymethylene-8-alkylthio-10-methylthio pyrimido [5,4-e]-1,2,triazole [1,5-c] pyrimidine possessing herbicidal activity and its preparation method

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102399225A (en) * 2011-11-28 2012-04-04 江西师范大学 3-fluorine-containing substituted benzamido-3,4-dihydro-4-imide-5-methylthio-7-ethylthio pyrimido[4,5-d]pyrimidine with herbicidal activity and preparation method thereof
CN102399226A (en) * 2011-11-28 2012-04-04 江西师范大学 3-substituted benzamido-3,4-dihydro-4-imine-5-methylmercapto-7-alkylthio pyrimido [4,5-d] pyrimidine with herbicidal activity and preparation method thereof
CN102491977A (en) * 2011-11-28 2012-06-13 江西师范大学 1-substituted benzene oxymethylene-8-alkylthio-10-methylthio pyrimido [5,4-e]-1,2,triazole [1,5-c] pyrimidine possessing herbicidal activity and its preparation method

Also Published As

Publication number Publication date
CN107400136A (en) 2017-11-28

Similar Documents

Publication Publication Date Title
TW200900386A (en) Diaminopyrimidines as fungicides
CA2338827A1 (en) Fused heterocyclic dicarboxylic acids diamide derivatives or salts thereof, herbicide and method for using the same
GB1587938A (en) Thiadiazolotriazinediones
CN103664808A (en) Aryl triazole compound containing chlorinated cyclopropane and preparation method and application thereof
CN107400136B (en) 2- substituted benzene oxygen methylene pyrimido [5,4-e] -1,2,4- triazol [1,5-c] pyrimidine and preparation method thereof
CN101323617B (en) 2,3,4,7-polysubstituted naphthyridine [4,3-d] pyrimidine derivates with sterilization activity and preparation thereof
CN109020916B (en) Substituted benzothiazole C2 alkylated derivative and application thereof
CN102491977B (en) 1-substituted benzene oxymethylene-8-alkylthio-10-methylthio pyrimido [5,4-e]-1,2,triazole [1,5-c] pyrimidine possessing herbicidal activity and preparation method thereof
CN104072455A (en) 6-aryloxy acetoxy aurone compound and application thereof on pesticide
CN104311598A (en) Phosphate compound containing 1,2,3-triazole ring as well as preparation method and application thereof
CN101775018A (en) Substituted 1H pyrazolo [3,4-d] pyrimidin-4(5H)-ketone derivatives with weeding activity and preparation thereof
JPH02273675A (en) 2,3-substituted 1,8-naphthylidine and herbicide containing that compound
WO2018205048A1 (en) Preparation method for new green sulfonylurea-type herbicide with controllable soil degradation rate, and study and use of same with regard to soil degradation
CN108059613B (en) Pyrazole amide compound and application thereof
CN102993105A (en) 1-methyl-2, 4-quinazoline diketone derivative and preparation method and application thereof
CN102835394A (en) Application of 2, 4-dichlorphenoxy acetyl-containing dihydrazide compound as herbicide
CN105859698A (en) N-(oxo-ethyl)-2-[4-(pyridine-2-yl-oxy)phenoxy]amide derivative
CN113549053A (en) Pyrazoloquine (azolyl) ether compound and application thereof
CN104356123A (en) 1,2,4-triazole Mannich base derivatives containing substituted piperazidine, and preparation method and application thereof
CN102399225B (en) 3-fluorine-containing substituted benzamido-3,4-dihydro-4-imide-5-methylthio-7-ethylthio pyrimido[4,5-d]pyrimidine with herbicidal activity and preparation method thereof
JPS62230782A (en) Imidazoline derivative, production thereof and herbicide
CN106008469A (en) 4-amino-5-[3-substituted phenoxymethylene-1H-1,2,4-triazole]pyrimidine and preparation method thereof
CN102399226B (en) 3-substituted benzamido-3,4-dihydro-4-imine-5-methylmercapto-7-alkylthio pyrimido [4,5-d] pyrimidine with herbicidal activity and preparation method thereof
CN103694180B (en) Pyrimidine-5-formic ether compounds and preparation method thereof and application
CN100436455C (en) Substitute 2,3-dihydrogen thiazole [4,5-d] pyrimidine-7(6H)- ketone (imines) having weed removal active and preparation thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
CB03 Change of inventor or designer information

Inventor after: Wang Tao

Inventor after: Xiong Fei

Inventor after: Xiong Gengming

Inventor after: Wu Xiaosheng

Inventor after: Zhao Anlin

Inventor after: Yu Weijie

Inventor before: Wang Tao

Inventor before: Xiong Gengming

Inventor before: Wu Xiaosheng

Inventor before: Zhao Anlin

Inventor before: Yu Weijie

CB03 Change of inventor or designer information
GR01 Patent grant
GR01 Patent grant